2-[(E)-hexadec-9-en-11-ynoxy]oxane | 176784-61-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-[(E)-hexadec-9-en-11-ynoxy]oxane
• CAS: 176784-61-5
• 化学式: C₂₁H₃₆O₂
• 分子量: 320.516
• InChiKey: PWEHSAVODPIUNR-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(E)-hexadec-9-en-11-ynoxy]oxane 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 以51.4 g的产率得到(9E)-hexadecen-11-yn-1-ol
  参考文献：
  名称：

  Passaro, Linda C.; Webster, Francis X., Synthesis, 2003, # 8, p. 1187 - 1190

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-10-碘-9-十一碳烯-1-醇 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 对甲苯磺酸 、 二异丙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.0h， 生成 2-[(E)-hexadec-9-en-11-ynoxy]oxane
  参考文献：
  名称：

  Sex attractant pheromone of the pecan nut casebearer (Lepidoptera: Pyralidae)

  摘要：

  A female-produced sex pheromone for the pecan nut casebearer, Acrobasis nuxvorella Neunzig, has been identified from pheromone gland extracts of calling female moths. The compound (9E,11Z)-hexadecadienal [(9E,11Z)-16:Ald] was identified by coupled GC-EAD and retention time matches with a synthetic standard on four capillary GC columns of different polarities. Corroboration of the identification of (9E, 11Z)-16:Ald by other analytical chemistry methods was not possible due to the minute quantities of pheromone extracted (<1 picogram/female). In field studies, gray rubber septa impregnated with 100 mu g of synthetic (9E,11Z)-16:Ald were attractive to male moths, whereas higher and lower doses were less attractive. The homologous (9E,11Z)-15:Ald was also slightly attractive, while the more highly conjugated analogues, (9E,11Z,13Z)- and (9E, 11Z,13E)-16:Ald, were not. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00010-7

文献信息

• 1-HALOALKADIENE AND A PROCESS FOR PREPARING THE SAME AND A PROCESS FOR PREPARING (9e, 11z)-9,11-HEXADECADIENYL ACETATE
  申请人：SHIN-ETSU CHEMICAL CO., LTD.

  公开号：US20190322614A1

  公开（公告）日：2019-10-24

  A process to prepare (9E,11Z)-9,11-hexadecadienyl acetate with a good yield and high purity of the general formula (1): CH 3 —(CH 2 ) 3 —CH═CH—CH═CH—(CH 2 ) a —X.=The process includes a step of conducting a Wittig reaction between a haloalkenal of the general formula (2): OHC—CH═CH—(CH 2 ) a —X, and a triarylphosphonium pentylide of the general formula (3): CH 3 —(CH 2 ) 3 —CH − —P + Ar 3 , to obtain the 1-haloalkadiene, and the use of a (7E,9Z)-1-halo-7,9-tetradecadiene obtained by the process for a process of preparing (9E, 11Z)-9,11-hexadecadienyl acetate.

  一种制备（9E,11Z）-9,11-十六烯基乙酸酯的方法，具有良好产率和高纯度，通式如下（1）：CH3—(CH2)3—CH═CH—CH═CH—( )a—X。该方法包括进行维特格反应的步骤，反应物为通式（2）：OHC—CH═CH—( )a—X的卤代烯醛，与通式（3）： —( )3—CH−—P+Ar3的三芳基膦五元阴离子，以获得1-卤代烯烃，并利用该方法获得的（7E,9Z）-1-卤代-7,9-十四烯烃，用于制备（9E,11Z）-9,11-十六烯基乙酸酯的方法。
• PROCESS FOR PREPARING (9e, 11z)-9,11-HEXADECADIENAL
  申请人：SHIN-ETSU CHEMICAL CO., LTD.

  公开号：US20190322605A1

  公开（公告）日：2019-10-24

  An efficient process for preparing (9E,11Z)-9,11-hexadecadienal of formula (4) is provided. The process includes at least steps of: conducting a nucleophilic substitution reaction between an (8E,10Z)-8,10-pentadecadienyl magnesium halide derived from an (8E,10Z)-1-halo-8,10-pentadecadiene of (1): and an orthoformate ester (2) to thereby prepare a (9E, 11Z)-1,1-dialkoxy-9, 11-hexadecadiene (3): and hydrolyzing the (9E, 11Z)-1,1-dialkoxy-9,11-hexadecadiene (3) to obtain (9E, 11Z)-9,11-hexadecadienal (4).

  提供了一种制备式（4）的（9E，11Z）-9,11-十六烷二烯醛的高效过程。该过程包括至少以下步骤：将来自于（1）的（8E，10Z）-1-卤代-8,10-十五碳二烯制备的（8E，10Z）-8,10-戊二烯基镁卤化物与正甲酸酯（2）之间进行亲核取代反应，从而制备（9E，11Z）-1,1-二烷氧基-9,11-十六烷二烯烃（3），并将（9E，11Z）-1,1-二烷氧基-9,11-十六烷二烯烃（3）水解以得到（9E，11Z）-9,11-十六烷二烯醛（4）。
• 1-HALOALKADIENE AND PROCESS FOR PREPARING THE SAME AND A PROCESS FOR PREPARING (9E,11Z)-9,11-HEXADECADIENYL ACETATE
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：EP3556742A1

  公开（公告）日：2019-10-23

  The object of the invention is to prepare (9E,11Z)-9,11-hexadecadienyl acetate with a good yield and high purity. The present invention provides a process for preparing a 1-haloalkadiene of the general formula (1): CH3-(CH2)3-CH=CH-CH-CH-(CH2)a-X, comprising a step of conducting a Wittig reaction between a haloalkenal of the general formula (2): OHC-CH=CH-(CH2)a-X, and a triarylphosphonium pentylide of the general formula (3): CH3-(CH2)3-CH--P+Ar3, to obtain the 1-haloalkadiene, and the use of a (7E,9Z)-1-halo-7,9-tetradecadiene obtained by the process for a process of preparing (9E,11Z)-9,11-hexadecadienyl acetate.

  本发明的目的是制备收率高、纯度高的(9E,11Z)-9,11-十六碳二烯乙酸酯。 本发明提供了一种制备通式（1）的 1-卤代碳二烯的工艺：CH3-(CH2)3-CH=CH-CH-CH-( )a-X，包括在通式(2)的卤代烯醛之间进行维蒂希反应的步骤：OHC-CH=CH-( )a-X的卤代烯醛与通式(3)的三芳基戊基鏻之间进行威蒂什反应： -( )3-CH--P+Ar3之间的反应，得到1-卤代烷二烯，并将通过该工艺得到的(7E,9Z)-1-卤代-7,9-十四烷二烯用于制备(9E,11Z)-9,11-十六烷二烯乙酸酯的工艺中。
• PROCESS FOR PREPARING (9E,11Z)-9, 11-HEXADECADIENAL
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：EP3556743A1

  公开（公告）日：2019-10-23

  The object of the invention is to provide an efficient process for preparing (9E,11Z)-9,11-hexadecadienal. The present invention provides a process for preparing (9E,11Z)-9,11-hexadecadienal (4), said process comprising at least steps of: conducting a nucleophilic substitution reaction between an (8E,10Z)-8,10-pentadecadienyl magnesium halide derived from an (8E,10Z)-1-halo-8,10-pentadecadiene (1) and an orthoformate ester (2) to thereby prepare a (9E,11Z)-1,1-dialkoxy-9,11-hexadecadiene (3); and hydrolyzing the (9E,11Z)-1,1-dialkoxy-9,11-hexadecadiene (3) to obtain (9E,11Z)-9,11-hexadecadienal (4).

  本发明的目的是提供一种制备(9E,11Z)-9,11-十六碳二烯醛的高效工艺。 本发明提供了一种制备(9E,11Z)-9,11-十六碳二烯醛（4）的工艺，所述工艺至少包括以下步骤：在由(8E,10Z)-1-卤代-8,10-十五碳二烯(1)衍生的(8E,10Z)-8,10-十五碳二烯镁卤化物和原甲酸酯(2)之间进行亲核取代反应，从而制备(9E,11Z)-1,1-二烷氧基-9,11-十六碳二烯(3)；水解 (9E,11Z)-1,1-二烷氧基-9,11-十六碳二烯 (3)，得到 (9E,11Z)-9,11-十六碳二烯醛 (4)。
• Process for preparing (9e, 11z)-9,11-hexadecadienal
  申请人：SHIN-ETSU CHEMICAL CO., LTD.

  公开号：US10618862B2

  公开（公告）日：2020-04-14

  An efficient process for preparing (9E,11Z)-9,11-hexadecadienal of formula (4) is provided. The process includes at least steps of: conducting a nucleophilic substitution reaction between an (8E,10Z)-8,10-pentadecadienyl magnesium halide derived from an (8E,10Z)-1-halo-8,10-pentadecadiene of (1): and an orthoformate ester (2) to thereby prepare a (9E, 11Z)-1,1-dialkoxy-9, 11-hexadecadiene (3): and hydrolyzing the (9E, 11Z)-1,1-dialkoxy-9,11-hexadecadiene (3) to obtain (9E, 11Z)-9,11-hexadecadienal (4).

  一种制备式 (4) 的 (9E,11Z)-9,11-十六碳二烯醛的高效工艺 的高效工艺。该工艺至少包括以下步骤：在由(1)的(8E,10Z)-1-卤代-8,10-十五碳二烯衍生的(8E,10Z)-8,10-十五碳二烯卤化镁之间进行亲核取代反应： 和原甲酸酯 (2) 从而制备出 (9E，11Z)-1,1-二烷氧基-9，11-十六碳二烯 (3)： 并水解 (9E，11Z)-1,1-二烷氧基-9,11-十六碳二烯 (3)，得到 (9E，11Z)-9,11-十六碳二烯醛 (4)。